3-(4-chlorophenoxy)phenol | 70870-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorophenoxy)phenol
• 英文别名: 3-(4-Chlorphenoxy)-phenol
• CAS: 70870-50-7
• 化学式: C₁₂H₉ClO₂
• 分子量: 220.655
• InChiKey: JQEGWOITLFBLCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenoxy)phenol 在 吡啶 、 水 、 potassium carbonate 、 caesium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.0h， 生成 (1-benzyl-5-{3-[3-(4-chlorophenoxy)phenoxy]propoxy}-1H-indol-3-yl)acetic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a series of alkoxy-3-indolylacetic acids as peroxisome proliferator-activated receptor γ/δ agonists

  摘要：

  A series of alkoxy-3-indolylacetic acid analogs has been discovered as peroxisome proliferator-activated receptor (PPAR) agonists. Structure-activity relationship study indicated that PPAR alpha/gamma/delta activities were dependent on the nature of the hydrophobic group, the attachment position of the alkoxy linker to the indole ring, and N-alkylation of indole nitrogen. Some compounds presented significant PPAR gamma/delta activity and molecular modeling suggested their putative binding modes in the ligand binding domain of PPAR gamma. Of these, compound 51 was selected for in vivo study via an evaluation of microsomal stability in mouse and human liver. Compound 51 lowered the levels of fasting blood glucose, insulin, and HbA1c without gain in body weight in db/db mice. When compound 51 was treated, hepatic triglycerides level and the size of adipocytes in white adipose tissue of db/db mice were also reduced as opposed to treatment with rosiglitazone. Taken together, compound 51 shows high potential warranting further studies in models for diabetes and related metabolic disorders and may be in use as a chemical tool for the understanding of PPAR biology. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.046
• 作为产物：
  描述：

  1-(4-氯苯氧基)-3-甲氧基苯 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到3-(4-chlorophenoxy)phenol
  参考文献：
  名称：

  神经元一氧化氮合酶亲脂尾单阳离子抑制剂的基于结构的设计、合成和生物学评价

  摘要：

  神经元一氧化氮合酶（nNOS）的选择性抑制剂有潜力发展成新的神经退行性疾病疗法。最近，我们描述了基于顺式吡咯烷药效团的新型 nNOS 抑制剂（ 1a和1b ）的发现。这些化合物和相关化合物被发现具有较差的血脑屏障渗透性，可能是因为分子中含有碱性氮。在此，利用与nNOS结合的1a、b的晶体结构，在对接实验的基础上设计了一系列单阳离子化合物。合成并评估了这些化合物抑制神经元一氧化氮合酶的能力。尽管这些化合物与结合至 nNOS 的1a、b具有极好的重叠，但它们表现出较低的效力。这是因为它们以正常方向而不是计算机建模中使用的预期翻转方向结合在 nNOS 活性位点中。联苯或苯氧基苯基尾部无序，不能形成良好的蛋白质-配体相互作用。这些研究证明了侧链尾部和第二个碱性氨基的大小和刚性对于 nNOS 结合效率的重要性以及疏水尾部对于 nNOS 活性位点构象定向的重要性。

  DOI：

  10.1016/j.bmc.2010.06.074

文献信息

• [EN] ARYL-SUBSTITUTED HETEROCYCLIC UREA MODULATORS OF FATTY ACID AMIDE HYDROLASE<br/>[FR] MODULATEURS HETEROCYCLIQUES A BASE D'UREE A SUBSTITUTION ARYLE DE L'HYDROLASE DES AMIDES D'ACIDES GRAS (FAAH)
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2010141809A1

  公开（公告）日：2010-12-09

  Certain aryl-substituted heterocyclic urea compounds are described, which are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity, such as anxiety, pain, inflammation, sleep disorders, eating disorders, energy metabolism disorders, and movement disorders (e.g., multiple sclerosis).

  描述了某些含芳基取代的杂环脲化合物，这些化合物可用作FAAH抑制剂。这些化合物可用于制备药物组合物，并用于治疗由脂肪酰胺水解酶(FAAH)活性介导的疾病状态、紊乱和症状，如焦虑、疼痛、炎症、睡眠障碍、进食障碍、能量代谢障碍和运动障碍(例如多发性硬化)。
• ARYL-SUBSTITUTED HETEROCYCLIC UREA MODULATORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Breitenbucher J. Guy

  公开号：US20120088741A1

  公开（公告）日：2012-04-12

  Certain aryl-substituted heterocyclic urea compounds are described, which are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity, such as anxiety, pain, inflammation, sleep disorders, eating disorders, energy metabolism disorders, and movement disorders (e.g., multiple sclerosis).

  本文描述了某些芳基取代杂环脲类化合物，它们可用作FAAH抑制剂。这些化合物可用于制备药物组合物和治疗由脂肪酸酰胺水解酶（FAAH）活性介导的疾病状态、疾病和病情的方法，例如焦虑、疼痛、炎症、睡眠障碍、进食障碍、能量代谢障碍和运动障碍（例如多发性硬化症）。
• Aryl-substituted heterocyclic urea modulators of fatty acid amide hydrolase
  申请人：Breitenbucher J. Guy

  公开号：US08901111B2

  公开（公告）日：2014-12-02

  Certain aryl-substituted heterocyclic urea compounds are described, which are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity, such as anxiety, pain, inflammation, sleep disorders, eating disorders, energy metabolism disorders, and movement disorders (e.g., multiple sclerosis).

  本文描述了某些芳基取代的杂环脲类化合物，其可用作FAAH（脂肪酸酰胺水解酶）抑制剂。这些化合物可用于制备药物组合物和治疗疾病状态、障碍和由FAAH活性介导的情况的方法，如焦虑、疼痛、炎症、睡眠障碍、进食障碍、能量代谢障碍和运动障碍（例如多发性硬化症）。
• TROPANE DERIVATIVES USEFUL AS PESTICIDES
  申请人：Selles Patrice

  公开号：US20100331348A1

  公开（公告）日：2010-12-30

  Compounds of formula (I) wherein the substituents have the meanings assigned to them in claim 1, are useful as pesticides.

  式(I)中的化合物，其中取代基具有在权利要求书1中分配给它们的含义，可用作杀虫剂。
• A mild alternative to the classical Ullmann coupling for preparation of 3-aryloxy phenols
  作者：Bhawyanth Duvvuru、Dinara Amankulova、Sébastien Gauden、Théo Haffemayer、Derrick L.J. Clive

  DOI：10.1016/j.tet.2023.133264

  日期：2023.3

  formed by the action of DBU on 2-bromo-3-(aryloxy)cyclohex-2-en-1-ones which are readily available from 3-chlorocyclohex-2-en-1-ones in two steps: replacement of the chlorine by an aryloxy group (ArOH, K2CO3, refluxing acetone or DMF at 100 °C) and bromination (NBS, DMF, room temperature). The procedure offers a mild alternative to the classical Ullmann reaction and does not require any metal catalyst

  m eta -(Aryloxy)phenols 由 DBU 与 2-bromo-3-(aryloxy)cyclohex-2-en-1-ones 作用形成，后者很容易从 3-chlorocyclohex-2-en-1-ones 中获得两个步骤：用芳氧基取代氯（ArOH、K 2 CO 3、在 100 °C 下回流丙酮或 DMF）和溴化（NBS、DMF、室温）。该过程提供了一种温和的替代经典乌尔曼反应的方法，不需要任何金属催化剂。如果原始苯酚 (ArOH) 带有供电子基团，则该方法效果很好，但当取代基吸电子时，芳构化步骤 (DBU) 会伴随 ArO 单元的一些损失。